Collect. Czech. Chem. Commun. 1990, 55, 2677-2684

The synthesis and X-ray structure of 3,7-diiododibenzosuberone. Synthesis of 3,7-diiodoamitriptyline

Ladislav Lešetickýa, Stanislav Smrčekb, Vladimír Svátaa, Jana Podlahovác, Jaroslav Podlahaa and Ivana Císařovád

a Department of Organic and Nuclear Chemistry, Charles University, 128 40 Prague 2
b Institute of Biotechnology, Charles University, 128 40 Prague 2
c Department of Inorganic Chemistry, Charles University, 128 40 Prague 2
d Institute of Physics, Czechoslovak Academy of Sciences, 180 40 Prague 8


The preparation of iodinated tricyclic antidepressive drug amitriptyline as the substrate for isotopic exchange labelling is described. Direct iodination of 10,11-dihydro-5H-dibenzo[a,d]-cycloheptene-5-one leads mainly to 3,7-diiododerivative (III). Its structure was confirmed by means of single crystal X-ray diffraction analysis: monoclinic, P21/c; a = 13.315(2), b = 7.852(1), c = 13.584(2) Å, β = 103.67(2)°, Z = 4, R = 0.064 for 2 474 observed independent reflections. Iodinated ketone was transformed to 3,7-diiodo-5-(3-N,N-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]-cycloheptene (diiodoamitriptyline), by the reaction with dimethylaminopropylmagnesiumchloride and dehydration of the resulting alcohol. The product was isolated as hydrogen oxalate salt.